Aggregation-Induced Emission and Sensing Characteristics of Triarylborane-Oligothiophene-Dicyanovinyl Triads

The design, synthesis and aggregation‐induced emission properties of a new series of triarylborane–oligothiophene–dicyanovinyl (DCV) conjugates 4–6 (A–D–A’ type molecular configuration) are reported. The optical properties of 4–6 can be modulated by judiciously varying the number of thiophene units...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-11, Vol.22 (48), p.17215-17225
Main Authors: Kumar, George Rajendra, Sarkar, Samir Kumar, Thilagar, Pakkirisamy
Format: Article
Language:English
Subjects:
Agglomeration
aggregation-induced emission enhancement
anion discriminators
Anions
Chemistry
Coating
Colorimetry
Cyanides
Emission
Filter paper
fluorescence
Media
Optical properties
sensors
Spacer
Spacers
Strip
triarylborane
Viscosity
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Summary:The design, synthesis and aggregation‐induced emission properties of a new series of triarylborane–oligothiophene–dicyanovinyl (DCV) conjugates 4–6 (A–D–A’ type molecular configuration) are reported. The optical properties of 4–6 can be modulated by judiciously varying the number of thiophene units between electron deficient boryl and dicyanovinyl units. Compound 6 with terthiophene spacer showed highly red‐shifted absorption and emission compared to 5 and 4 with bithiophene and monothiophene spacers, respectively. Compounds 5 and 6 show aggregation‐induced emission enhancement in water/THF mixtures. Compounds 5 and 6 also showed solvent viscosity dependent emission characteristics. All the three compounds show distinct optical responses for small anions such as fluoride and cyanide. Filter paper strips coated with compounds 5 and 6 can detect F− and CN− in aqueous media with different colorimetric responses. Hazard detectors: The design and synthesis of a series of triarylborane–oligothiophene–dicyanovinyl triads 4–6 (A–D–A’) is reported (see figure). The optical properties of 4–6 were elegantly modulated by judiciously varying the number of thiophenyl spacers between the acceptors. Compounds 5 and 6 are AIE active and also exhibit significant luminescence in a PMMA matrix. Filter paper strips coated with compounds 5 and 6 can detect F− and CN− in aqueous media with different colorimetric responses.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201603349